Phosphorus pentachloride → HCID 24976598, compound

HRID 1414511Notes

Reaction equation

HRID 1414511 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([O-:16])=O.P(Cl)(Cl)(Cl)(Cl)Cl>C1C=CC=CC=1>[C:12]([CH2:13][C:14]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10])=[O:16])([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 69157Benzenamine, N-methyl-2-nitro-HCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 24976598HCID 24976598, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

75 g of N-methyl o-nitro aniline and 70 g of monoethyl malonate (obtained according to M. FREUND, Ber. 17, 780, 1 884) are dissolved in 550 c.C. of benzene, the solution is agitated and 106 g of phosphorus pentachloride are added, while maintaining the temperature at 20°-23° C; this is agitated for three hours at room temperature, then heated for one hour at 70° C; an yellow precipitate forms, which dissolves again, giving an orange solution; a water-ice mixture is added, while agitating, to obtain a volume of 1,500 c.c., keeping the temperature at 30° C; the benzene phase is decanted off, washed with water, then with a saturated aqueous solution of sodium bicarbonate and finally with water, dried over sodium sulfate and evaporated under reduced pressure; the residue is purified by recrystallisation in the xylol-petroleum ether mixture (2,5-1). The compound melts at 54°-55° C. Analysis: C12H14N2O5 = 266.25; Calculated: C % 54.13; H % 5.30; N % 10.52; Found: 54.02; 5.23; 10.77.

Workup

  1. temperaturewhile maintaining the temperature at 20°-23° C
  2. temperatureheated for one hour at 70° C
  3. dissolutionan yellow precipitate forms, which dissolves again
  4. customgiving an orange solution
  5. stirringwhile agitating
  6. customto obtain a volume of 1,500 c.c
  7. customat 30° C
  8. customthe benzene phase is decanted off
  9. washwashed with water
  10. dry with materialwith a saturated aqueous solution of sodium bicarbonate and finally with water, dried over sodium sulfate
  11. customevaporated under reduced pressure
  12. customthe residue is purified by recrystallisation in the xylol-petroleum ether mixture (2,5-1)

Sources & evidence

ORD record
ord-e2bde6a99dd04eaaa0683e87315af7aa
Source dataset
uspto-grants-1977_01
Patent number
US04001408

Reaction notes

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